Visible-Light-Induced Direct Photoamination of BODIPY Dyes with Aqueous Ammonia

By taking advantage of their strong absorption ability, visible-light-induced direct photoamination of BODIPY dyes with aqueous ammonia was developed to give structurally diverse α-amino BODIPYs. The excited state of BODIPYs possessed higher electron affinity than the ground state and thus showed la...

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Bibliographic Details
Published in:Organic letters 2023-10, Vol.25 (42), p.7650-7655
Main Authors: Wang, Dandan, Wang, Long, Guo, Xing, Zhang, Xiankang, Ma, Juan, Kang, Zhengxin, Li, Zhong-Yuan, Jiao, Lijuan, Hao, Erhong
Format: Article
Language:English
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Summary:By taking advantage of their strong absorption ability, visible-light-induced direct photoamination of BODIPY dyes with aqueous ammonia was developed to give structurally diverse α-amino BODIPYs. The excited state of BODIPYs possessed higher electron affinity than the ground state and thus showed largely enhanced reactivity toward weak nucleophile of ammonia. Those α-amino BODIPYs are valuable synthetic intermediates and have been successfully demonstrated in several post-transformation reactions. The work indicates that photoreaction is an excellent alternative to conventional functionalization of this popular fluorophore.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02962